This invention is concerned with a microbial process for the production of compositions of matter containing unsaturated lactones.
Considerable time and effort have been expended by microbiologists in the search for better processes for the production of unsaturated lactones; and more generally lactones per se. U.S. Pat. No. 3,076,750 discloses a method of preparing certain optically active lactones and the corresponding hydroxycarboxylic acids by microbial reduction of ketocarboxylic acids. The metabolism of ricinoleic acid by some Candida strains was investigated by Okui, et al (J.Biochemistry, 54,536-540, 1963) who showed that gamma hydroxydecanoic acid was an intermediate in the oxidative degradation of ricinoleic acid. However, only trace amounts of gamma hydroxydecanoic acid were recovered from the fermentation medium due to the metabolysis of gamma hydroxydecanoic acid upon completion of the fermentation, and the toxicity of ricinoleic acid to the microorganism, which limits the amount of substrate that can be used.
U.S. Pat. No. 4,560,656 provided a method of producing optically active gamma hydroxydecanoic acid comprising culturing or incubating a microorganism capable of hydrolyzing castor oil, and effecting beta-oxidation of the resulting hydrolysate in the presence of castor oil, to produce gamma hydroxydecanoic acid.
U.S. Pat. No. 4,560,656 also provided a method of producing optically active gamma hydroxydecanoic acid comprising enzymatically hydrolyzing castor oil using lipase to form an enzymatic hydrolysate and culturing or incubating a microorganizm capable of effecting beta-oxidation of the enzymatic hydrolysate in the presence of said hydrolysate to produce gamma hydroxydecanoic acid.
U.S. Pat. No. 4,560,656 also provided a method of producing optically active gamma hydroxydecanoic acid comprising culturing or incubating a microorganism capable of hydrolyzing castor oil and a microogranism capable of effecting beta-oxidation of castor oil hydrolysate in the presence of castor oil to produce gamma hydroxydecanoic acid.
European Published Patent Application 258993 published on Apr. 9, 1988 discloses a process for the production of optically active gamma hydroxydecanoic acid suitable for conversion to optically active gamma decalactone. The process covers steps of:
(a) culturing sporobolomyces odorous; and/or rhodotorula glutinis on a medium containing a ricinoleic acid sources at 15.degree.-35.degree. C. at a pH of 3-9 and optionally; and
(b) lactonizing the resulting gamma hydroxydecanoic acid to gamma decalactone.
Nothing in the prior art however discloses the ability by means of fermentation to create a novel mixture of unsaturated lactones together with, optionally, gamma decalactone found to be useful in augmenting or enhancing the organoleptic properties of consumable materials.
In the flavor and fragrance art, a need has arisen for the development and efficient production of naturally occurring lactones which have heretofor been found to be useful and necessary in the creation of flavor formulations used in augmenting or enhancing the aroma or taste of foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos and smoking tobaccos and also useful in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, fabric softener compositions, fabric softener articles, hair preparations, cosmetic powders and the like).
Although U.S. Pat. No. 4,560,656 has partially fulfilled the need for provision of saturated gamma decalactone defined according to the structure: ##STR8## nothing in the prior art sets forth the creation of unsaturated lactones defined generically according to the structure: ##STR9## and defined more specifically according to the structures; ##STR10##